For how long should a CEO continue being the head of products?

Roughly for me, for as long as it’s about a 10-hour a week job. Or often, maybe only up to $3m-$5m in ARR or so.

In SaaS at least, founders make two mistakes:

First, try to hire a full-time “head of product” once the product gets complex. Once your product has 50–100 workflows, dozens of use cases, 100s or 1000s of customers, etc. … it’s just too much to hack and juggle informally. My rough rule of thumb is somewhere between $3m and $5m in ARR in SaaS most products just get too complicated to hack product anymore. You’ll ship better prioritized features, with happier customers, with better trade-offs, with a full-time head of product. CEOs that hang on too long here start shipping features and products that are no longer force-ranked the way they should be. And the key is to hire a true head of product. Someone that can own it, and in the past, has owned a product. If you hire someone too junior, you get a project manager but not enough of an owner here.

And second, later, CEOs wait too long to give up on being the product visionary. Hopefully, the CEO is always the strategic visionary, forever. But at some point, the product itself gets so deep and rich, and the markets evolve so much, and the customer needs are so varied and nuanced once you dig in deep … that the founders’ original product vision becomes too simplistic, too dated and stale. Every 5–6 years or so in most cases, everything in the market has changed, and the product has evolved so far that the Day 0 vision is very dated. At this stage, founders need to let go and have the team own the product vision — not them. The founders still are the heart of the corporate strategy. But the team is now spending 1000x more time with customers, with feature enhancements, with nuances on a product lines with 1000s of features … you have to let the team define 95% of The Future. And your job becomes more to set the direction, but not provide the directions.

So bring in more help, and let go a bit earlier than planned. It’s your idea, and your vision, but both of those need to evolve in the coming years.